Summerland Key, FL Homes for Sale under $500,000

/10
$499,000
- Land
63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(305) 834-4054

63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
/39
$485,000
- 1 Bed
- 1 Bath
- 754 Sq Ft
701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

Ian Calderwood

Bluescape Real Estate

(786) 551-4336

701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
/60
$487,500
- 2 Beds
- 1 Bath
- 667 Sq Ft
701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

Ian Calderwood

Bluescape Real Estate

(786) 981-9841

701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
/42
$499,999
- 2 Beds
- 2 Baths
- 873 Sq Ft
4 Coral Dr, Key West, FL 33040

Motivated Sellers - creative offers welcome!VA Assumable Rate at 3.5% for eligible Buyers!Enjoy your own slice of the Keys! This efficient 2-bedroom, 2-bath home offers comfort, functionality, and a wonderful outdoor lifestyle. The inviting floor plan flows easily between the living, dining, and kitchen areas, making everyday living and entertaining effortless. Step outside to a spacious back

Lindsay Ryan

EXP Realty LLC

(786) 981-3025

4 Coral Dr, Key West, FL 33040
/9
$450,000
- 2 Beds
- 1 Bath
- 460 Sq Ft
6 Beach Dr, Key West, FL 33040

Rare DOUBLE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot can be cleared providing huge wide water sunset views and the ability to add dockage with shallow boating access. Located in the Saddlebunch Keys, just 10 minutes from all of the superior dining and nightlife of Key West, Florida. Repair trailer that is on site under the 50% rule, or build your dream home

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(786) 756-8747

6 Beach Dr, Key West, FL 33040
/39
$499,000
- 2 Beds
- 2 Baths
- 618 Sq Ft
701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

Suzanne Moore Suzanne Moore Real Estate

701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042
/20
$465,000
- 1 Bed
- 1 Bath
- 799 Sq Ft
701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal.'1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room and 1 Updated Bathroom with walk in shower, glass doors, hand rail and built in bench, skylight, humidifier, light & exhaust fan. Bedroom has custom closet with built in drawers & sliding doors. The bonus room can

Rose Dell Keller Williams Key West Compass Realty

701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
/30
$430,000
- 2 Beds
- 1 Bath
- 415 Sq Ft
21857 Disturbed Pine Rd, Summerland Key, FL 33042

Acre Property! I've heard it said privacy is the ultimate luxury. Your Keys bungalow in the woods with a separate screened porch enclosure 13 X 18 plus a storge room 9 X 12. Connected to the house by a wood deck walkway. Artist retreat, man cave or maybe just because you love privacy and want an escape. Lots of potential. Are you handy! Additionally, there are 2 carports, Multiple storage areas.

Rose Dell Keller Williams Key West Compass Realty

21857 Disturbed Pine Rd, Summerland Key, FL 33042
/4
$400,000
- Land
- 1,400 Acres
- $286 per Acre
27378 Jamaica Ln, Summerland Key, FL 33042

ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

Patricia Borges Borges Realty Group LLC

27378 Jamaica Ln, Summerland Key, FL 33042
/47
$455,000
- Land
701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
/18
$499,000
- Land
701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

The Spottswood Team Truman & Co. (KW)

701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
/19
$465,000
- Land
701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
/21
$475,000
- 1 Bed
- 1 Bath
- 668 Sq Ft
701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
/30
$485,000
- 2 Beds
- 1.5 Baths
- 604 Sq Ft
701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
/56
$494,500
- 2 Beds
- 2 Baths
- 930 Sq Ft
30950 Witters Ln, Big Pine Key, FL 33043

Beautifully remodeled concrete home with impact windows on a generous lot in a quiet, private area of Big Pine Key in Doctor's Arm. This unique 2-bedroom, 2-bath residence offers a flexible layout that may appeal to those seeking separate living areas under one roof. The home features two distinct living spaces, each with its own kitchen and bathroom, providing versatility for extended family,

Wiebke Westedt LoKation Real Estate

30950 Witters Ln, Big Pine Key, FL 33043
/18
$470,000
- Land
701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
/3
$449,000
- Land
- 0.34 Acre
- $1,303,896 per Acre
Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

Oversized lot in gorgeous Sugarloaf Key with 15,000 Square feet ready for you to enter into the ROGO system. This sale comes with a ROGO Point Letter from Monroe County for 0 Disturbed Pine worth 24 points, giving you 44 points to enter into the ROGO system to build your dream home. Seller has done the Letter of Current Site Conditions with the County as well as engineering for a house, just

Pamela Stangler Expert Realty LLC

Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
/25
$469,000
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
27973 Snapper Ln, Little Torch Key, FL 33042

Welcome to your dream retreat by the sea! This beautifully renovated 2/2 offers the perfect blend of classic coastal charm and modern upgrades. Recently renovated with a new roof (2021), new doors and windows (2000), new AC units and updated paint throughout. This home is located in a serene waterfront community with an unlimited free-access boat launch located only minutes from the house. Enjoy

Bill Vaught (REO Vaught Realty LLC Vaught Realty

27973 Snapper Ln, Little Torch Key, FL 33042
/10
$450,000
- Land
30324 Frigate Ln, Big Pine Key, FL 33043

CLEARED WATERFRONT CORNER LOT IN TROPICAL BAY with active building permit! Build your dream CBS home in a wonderful subdivision. Building permit is good till 2028! Large dock already in place. 20' on short side and 55 feet on the long side. Seller financing possible.

Derrick Johnson Coco Plum Real Estate

30324 Frigate Ln, Big Pine Key, FL 33043
/46
$419,000
- 1 Bed
- 1 Bath
- 833 Sq Ft
701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

Jan Fritz Coldwell Banker Schmitt RE Co.

701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
/36
$450,000
- Land
701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and walkway,

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
/16
$499,000
- Land
- 0.44 Acre
- $1,141,020 per Acre
Vacant Lot Canal St, Big Pine Key, FL 33043

Prime Commercial Fishing Property in the Florida Keys!Discover a rare opportunity to own and operate a commercial fishing business in the coveted Commercial Fishing Special District of Big Pine, FL. This unique zoning allows unparalleled access to open water, making it a fisherman's paradise. Here are the highlights:- Buildable Property: Your vision can come to life with ease on this buildable

Sam Williams Coldwell Banker Schmitt Real Estate Co.

Vacant Lot Canal St, Big Pine Key, FL 33043
/30
$460,000
- 1 Bed
- 1 Bath
- 748 Sq Ft
701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
/46
$487,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
/52
$410,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
/17
$450,000
- Land
132 Blackbeard Rd, Little Torch Key, FL 33042

This beautiful oversized lot is located in Jolly Rogers Estates, Little Torch Key. Corner lot with two sides of canal front with some open water views. The seller said permit it ready to come out of ROGO.. Permit is for a 1227 sq ft 3 bedrooms & 2 baths, Modular Home. Buyer to finish the permitting process. Enjoy quick boating access to the Gulf and Atlantic. Dolphin Marina is across the canal

Halley Haack Coldwell Banker Schmitt RE Co.

132 Blackbeard Rd, Little Torch Key, FL 33042
/11
$480,000
- Land
701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

Carmen Brake Waterfront Keys Realty Inc.

701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

Florida Monroe County Summerland Key

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In Summerland Key, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 27 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Summerland Key, FL and find the perfect fit for your homeownership goals.

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